Bis-triazinylamino-stilbene sulphonic acid compounds



United States Patent Ofitice 3,371,089

Patented Feb. 27, 1968 3371039 liminary experiments and the application of the com- BIS.TRIA I A 1 SULPHONIC pounds as brightening agents can be performed in the ACID COMPOUNDS usual nn r Heinrich Gold, Cologne-Stammheim, Erich Lehmann, The following examples serve to illustrate the lnventlon Burscheid, and Werner Theuer, Leverkusen, Germany, 5 without, however, limiting its scope; the parts given are assignors to Farbenfabriken Bayer Aktiengesellschaft, parts b i h Leverkusen, Germany, a German corporation Example 1 No Drawing. Filed July 28, 1964, Ser. N 0. 385,776

Claims Priority Zggg 1963 300 parts of crushed ice and 150 parts of water are dded to a solution of 37 arts of cyanuric chloride in 10 a P 6 Clalms' (Cl 260 240) 300 parts of acetone and the cyanuric chloride suspension The present invention relates to bis-triazinylaminothus obtained is treated with a solution of 41.4 parts of stilbene disulphonic acid compounds; more particularly the disodium salt of 4,4'-diaminostilbene-2,2-disulphonic it concerns bis-triazinylamino-stilbene disulphonic acid acid in 400 parts of water at a temperature of at most compounds of the general formula 5 C. The reaction solution is then adjusted to neutrality N N R-OCHzCH2-O(I'IJ (ll'NH CH=CHNH(|3 g-O-CHh-CEh-O-R' N N l N N $0 K $03K f XOsSCHaCHzN NGHz-CH2SO3X /r RI! In this formula R stands for an alkyl radical containing by the addition of an approximately percent soda 1 to 4 carbon atoms, and R represents hydrogen or an solution. As soon as the pH value no longer alters, the alkyl radical also containing 1 to 4 carbon atoms, While solution is treated with 32.5 parts of the sodium salt of X stands for hydrogen or the equivalent of a cation. B-N-methylaminoethane sulphonic acid in the form of a The bis-triaZinylamino-stilbene disulphonic acid com- 30 to percent aqueous solution, heated at 38-40 C. p f 9 the Presfillt lllventloff can be Obtalned y 6011- for two to three hours and then neutralised with a soda denslng 111 known manner and 111 y Sequence two mols solution. The tetrasodium salt of 4,4'-bis-(2-(N-methylof cyanuric chloride with one mol of 4,4'-diaminostilbene- 2,2-disulphonic acid, with two mols of a 2-alkoxy ethanol and with two mols of an optionally N-alkylated 2-aminoethane sulphonic acid and then optionally transforming the condensation products into salts, e.g. into the alkali aminoethane sulphonic acid)-4-chloro-l,3,5-triazinyl-(6)- amino)-stilbene-2,2-disulphonic acid thus formed is salted out by the addition of 500 parts of a saturated common salt solution, filtered off with suction and dried in vacuum at 30 to 40 C. 48 parts of this salt are then figgggiggTggig? 3:3 22; j fi f gg zi gfi added to a solution which was obtained by dissolving n 01 S; examples of the optionally N alkylated 40 2.3 parts of metallic sodium in 250 parts of glycol monoethane sulphonic acids are Z-methylamino, 2-ethylamino, methyl ether- The mlxture heated at 100 to 1050 C4 2-propylaminoand Z-butylamino ethane sulphonic acids. for four hours then Poured 500 Parts of water and The bis-triazinylamino-stilbene compounds of the intreated at room temperature Wlth 80 Parts of Common tio are very f l compounds I particular, h salt. The precipitate is filtered oif with suction and dried. can be used as brightening agents, for instance for bright- The bis-triaZinylamino-stilbene compound thus obtained ening textiles, especially textiles of Wool and of synthetic corresponds to the formula polyamides. The brightening effect attained possesses If instead of glycol monomethylether an equivalent good wetand light-fastnesses and is distinguished by a amount of glycolmonoethyl ether or glycolmonopropyl high brillance. The bis-triazinylamino-stilbene comether is used or if for the 18-N-methylarninoethane sulpounds of the present invention are further outstandingly phonic acid an equivalent amount of fl-N-butylaminosuitable for the brightening of acid-treated paper. The ethane sulphonic acid is substituted the following bisquantities of the compounds required for the individual triazinylamino-stilbene compounds can be obtained in an brightening purposes may be readily determined by preanalogous manner.

cent china clay, 2 percent resin size, and 4 percent 5 pound of the formula aluminium sulphate, is coated in a coating apparatus, e.g.,

in a glue press, with an aqueous solution which contains l per litre 3 grams of the first mentioned bis-triazinyl- R-OCHi-CHO-O CNHCH: amino-stilbene compound as brightening agent so that l l;

the liquid take up of the paper amounts to to 50 grams 3O SOBX of solution per square metre of surface. The paper is subsequently dried at 80 to 100 C. and then shows an XOaSCH2CHa-N outstanding brightening effect. 2

A similar brightening effect is obtained if one of the others aforesaid bis-triazinylamino-stilbene compounds is used as brightening agent in which R is alkyl containing 1-4 carbon atoms, R

is hydrogen or alkyl containing 1-4 carbon atoms, and

Example 2 X is hydrogen, an alkali metal or ammonium moiety.

A solution of 1 85 parts of cyanuric chloride in 1000 A compound of the formula parts of glycol monomethyl ether is treated with 168 parts 40 N of sodium bicarbonate and heated with good stirring to about 32 C. The carbon dioxide evolved by the reaction HZC O CH1 CH2 O (|3NH CH: is passed through a gas meter and measured. As soon as N N I about 23 litres of carbon dioxide have been released, the soaNa solution is cooled to room temperature. A solution of 186 1 parts of the disodium salt of 4,4'-diaminostilbene-2,2'-di- 2 sulphonic acid in 1400 parts of water are then added within 15 minutes, whereby the temperature rises to 34 to 36 C. After about half an hours reaction time, the pH value of the reaction solution is adjusted to 6.9 to 7.0 by the 3. A compound of the formula addition of about 25 parts of a 20 percent soda solution. 0 A solution of 150 parts of the sodium salt of fi-amino- CQHFCPCEGHPCPEE ethane sulphonic acid in 500 parts of water is then added N and the reaction mixture is heated at 9 6 to 98 C. for two 503m hours. After cooling to room temperature, the bis-triazinylamino-stilbene compound of the formula 2 I oH3o-o11zorn0- 1NHoH=oH-NH-o o-omom-oorn N N I l N N S0311 S0311 f f NHCHz-CHz-SO:N& NHOH CH;-SO Na is salted out by addition of 300 parts of common salt, 4. A compound of the formula then filtered off with suction and dried.

A fabric from a polycondensate of e-caprolactam is treated for 30 minutes at to C. at a liquor-to-goods N '1 ratio of 40:1 with an aqueous bath which contains per 0 litre 0.1 gram of the b1s-tr1az1nylam1no stilbene compound ll N mentioned above. The fabric is then rinsed with cold SOaNB water and dried in air. The fabric thus treated possesses I an outstanding degree of whiteness. 75 NaOaS-CH2CH2NCHa 2 5 S. A compound of the formula om-o-cm-c'm o-c c-nnc N-o.s-cu.-cm-x z-n-c.n.

6. A compound of the formula N cur-o-cu -cm-q-gzmg-Nu 6 References Cited 1 A FOREIGN PATENTS cn 43,527 9/1960 Poland. 6 528,443 7/1956 Canada. som'u 562,427 5/1958 Belgium.

1 JOHN D. RANDOLPH, Primary Examiner. 

1. A BIS-TRIAZINYLAMINO-STILBENE DISULPHONIC ACID COMPOUND OF THE FORMULA 